Pajamas Media received venture capital funding in November, 2005. Pajamas used this funding for its operations and marketing while expanding its news and opinion coverage. Investors in this round of financing included Aubrey Chernick, an angel investor and technology entrepreneur, James Koshland, a venture capitalist, and a partnership formed by DLA Piper Rudnick Gray Cary.[9] It rebranded as Open Source Media shortly thereafter and had a launch party that included a keynote address by former New York Times journalist Judith Miller, presentations from John Podhoretz of Commentary magazine, Andrew Breitbart, Elizabeth Hayt of the New York Times,David Corn of The Nation, and others. Less than a week after its official launch Open Source Media changed its name back to Pajamas Media after discovering that Public Radio International distributed a radio show called Open Source produced by Open Source Media, Inc.[10]

In September 2013, former congressman Allen West left PJ Media after he had an altercation with a female staffer and allegedly called her a "Jewish American princess."[14] West denied being fired and said he left voluntarily.[14]